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Substance Name: Sergeolide
RN: 82290-17-3
InChIKey: ZZKFDOQILIXHHH-OKNMSMBGSA-N

Note

  • Quassinoid from Simaroubaceae Picrolemma pseudocoffea.

Molecular Formula

  • C25-H28-O11

Molecular Weight

  • 504.485
 
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Names and Synonyms

Name of Substance

  • Sergeolide

Synonyms

  • BRN 4621448
  • New quassinoid sergeolide
  • NSC 344025
  • Sergeolide

Systematic Name

  • 3,13-Ethano-1H,10H-furo(3,4-c)furo(2',3':6,7)naphtho(2,3-b)pyran-3(3ah)-carboxylic acid, 4-(acetyloxy)-4,5,6a,7,7a,8,12a,13-octahydro-14,15-dihydroxy-8,12a-dimethyl-5,10-dioxo-, methyl ester, (3S-(3-alpha,3a-alpha,4-alpha,6a-alpha,7a-beta,8-beta,12a-alpha,13-alpha,13aS*,14S*,15R*))-

Registry Numbers

CAS Registry Number

  • 82290-17-3

System Generated Number

  • 0082290173

Structure Descriptors

InChI

1S/C25H28O11/c1-9-11-5-15(27)35-13(11)7-23(3)12(9)6-14-24-8-33-25(22(31)32-4,20(29)16(28)18(23)24)19(24)17(21(30)36-14)34-10(2)26/h5,7,9,12,14,16-20,28-29H,6,8H2,1-4H3/t9-,12+,14-,16-,17-,18-,19-,20+,23+,24-,25+/m1/s1

InChIKey

ZZKFDOQILIXHHH-OKNMSMBGSA-N

Smiles

C1(OC2=C[C@@]3([C@H]4[C@H]([C@@H]([C@@]5([C@H]6[C@@]4([C@@H](C[C@H]3[C@@H](C)C2=C1)OC(=O)[C@@H]6OC(=O)C)CO5)C(=O)OC)O)O)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 1800ug/kg (1.8mg/kg)   Planta Medica. Vol. 51, Pg. 20, 1985.